Sodium Carbonate → 5-Bromo-6-methoxy-isoquinoline

HRID 1436010

Reaction equation

HRID 1436010 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].[Br:17]Br.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[Br:17][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 110409786-Methoxyisoquinoline

Product 1

HCID 222265455-Bromo-6-methoxy-isoquinolineYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxyisoquinoline (2.38 g, 14.9 mmol) in dichloromethane (55 ml) was added AlCl3 (4.4 g, 33 mmol) under nitrogen at ambient temperature. The mixture was stirred for 30 min then Br2 (0.92 ml, 18 mmol) was added at 0° C. The mixture was stirred for 2 h, then poured into water and neutralised with solid Na2CO3. The mixture was filtered through celite and the filtrate extracted with dichloromethane and chloroform. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue on silica (eluent: 50-100% ethyl acetate in heptane) gave 5-bromo-6-methoxyisoquinoline (1.2 g, 34% yield).

Workup

  1. stirringThe mixture was stirred for 2 h
  2. filtrationThe mixture was filtered through celite
  3. extractionthe filtrate extracted with dichloromethane and chloroform
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-4515ddca052643cb85f5d871328f610f
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Linked notes

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